Helvetica Chimica Acta p. 237 - 261 (1987)
Update date:2022-08-04
Topics:
Seebach, Dieter
Juaristi, Eusebio
Miller, David D.
Schickli, Christof
Weber, Theodor
Chiral enolates of imidazolidinones and oxazolidinones from the title amino acids react with carbonyl compounds to afford the corresponding alcohols in excellent yields (see Scheme 5).Furthermore, the addition to aldehydes proceeds with high diastereoselectivity to give, after acid hydrolysis, threo-α-amino-β-hydroxy acids of high enantiomeric purity.Some of the threo-α-amino-β-hydroxy acids prepared in this work are the proteinogenic (S)-threonine (26), the naturally occuring (S)-3-phenylserine (28), and (S)-3-hydroxyleucine (27) as well as the unnatural (S)-4,4,4-rtifluorothreonine (30) and (S)-3-(4-pyridyl)serine (31).The N-methylamide of (2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoic acid (32), the uniqe amino acid in the immunosuppressive cyclosporine, was prepared by the new method.This report presents also information suggesting that both steric and stereoelectronic effects are responsible for the good stereoselectivities observed.
View MoreContact:+36(21)2523420
Address:Head office: 1102 Budapest, SZENT LASZLO TER 24/B. 1/1., HUNGARY / CHINA
Shanghai Yuking Water Soluble Material Tech Co., Ltd
Contact:86-21-68286299
Address:4F, 13B, No. 600, South Xinyuan Road 201306, Shanghai, China
Anhui New Star Pharmaceutical Development Co., Ltd
Contact:013956922763
Address:Floor 3, F9A, F Workshop, No.110 Kexue Road, High-Tech Development Zone, Hefei, Anhui ,China
Contact:+86-21-38228826
Address:Room 505 Building 2, No 3377 Kangxin Highway, Shanghai, Republic China
Jiangsu King Road New Materials Co., Ltd.
website:http://www.jskingroad.com
Contact:0519-85720726 0519-85720721 13584535752
Address:No.1,Weihua Road,Xinbei District,Changzhou City,Jiangsu Province
Doi:10.1021/jo01052a075
(1962)Doi:10.1002/adsc.201300211
(2013)Doi:10.3390/molecules23051154
(2018)Doi:10.1039/b717556f
(2008)Doi:10.1021/ja800738d
(2008)Doi:10.1016/j.poly.2007.11.020
(2008)